Lizz Winstead has had an enormous influence on popular culture. She dreamed up a new satirical genre on television when she created The Daily Show back in 1996. She was a co-founder of the Air America radio network and gave Rachel Maddow her first national audience. The woman has good instincts.
A standup comedian by trade, Winstead got her start in her native Minneapolis. She honed her skills in what she calls the “punk rock ghetto” of the early 1980s. She was part of an incredibly creative time in the Twin Cities: the Replacements, Soul Asylum, Hüsker Dü, New York Times writer David Carr, NPR’s Michele Norris (her roommate), and so many others hail from that scene. “We were all just oddballs trying to make it,” she says, “and had built a community based on taking a shot at our dreams.”
Winstead has a new book, Lizz Free or Die, coming out in May. In it, she writes about her early years, moving to New York City and embarking on her life’s work. Many of the essays reveal how she found her voice and the challenges she encountered along the way. She grew up in the Catholic Church and found a calling in comedy, two “big behemoths that are not particularly friendly to women or to building women’s careers,” she says.
The book also contains a very personal essay she wrote about getting pregnant the first time she had sex at seventeen. She stumbled into one of those Christian pregnancy centers that claims to be a clinic and present options, but offers only guilt and fear. She walked out.
She has been stumping for Planned Parenthood, raising money at shows across the country. Last year, she went on a fundraising circuit and got death threats. “I had to have a bodyguard the whole time I was on the Planned Parenthood tour,” she says.
I caught up with Winstead in Brooklyn, where she now lives. It was early March, and the nasty rhetoric on women’s health care was reaching an apex. Her Twitter feed, where she takes on the political nonsense of the day, was a source of humor when Rush Limbaugh was talking about sluts.
“I called my book Lizz Free or Die because I just wanted to simply try to pursue my dreams on my own terms,” she told me over lunch. “But I should’ve called it Fight to the Death, because that’s what it feels like. Is it ever going to stop? These weird obstacles that make no sense, that get in the way of women just simply for wanting to be not tortured in their own skin.”
Q: Why did you decide to write this book?
Lizz Winstead: At first, I thought, I don’t know if I have a book in me. But if I can inspire people and get them to understand that being different is OK, that you are going to have a way better life, great.
I liked music that was a little different, food that was a little different, clothes that were a little different. So I knew what I had to say wasn’t probably going to be some big massive thing embraced by the world, but I don’t really care.
Q: Was it hard to write the abortion story?
Winstead: I wrote it because it’s not extraordinary. I read the essay at the end of the Planned Parenthood shows I do. I’ve had anywhere between ten and thirty women come up to me at one single show and say, “I’ve had an experience very similar to that.”
It’s really valuable that people start talking. Then, when people are just demonizing women, they have to think of someone they know. And they have to say, “Wow, I like Ann. Ann’s not awful. Ann had an abortion.”
Q: It’s a personal story, but without people telling these personal stories, the shaming continues.
Winstead: The profound shame part of it is why I have a tendency to always talk about these issues in a sexual empowerment way. People say, completely validly, that birth control is also used for endometriosis and all this other stuff—that’s incredibly important. But that doesn’t take away the shaming part of it. Having sex is OK. And using birth control to have sex is OK.
Q: How do you manage to take politics seriously and not feed into the hate?
Winstead: Humor is super powerful. Whenever I’m writing, I think, if I make you laugh that means we are connected. You don’t laugh at people you don’t like. Maybe there’s a jumping off point.
Q: You went out on a Planned Parenthood tour last year and you are going out again this year. What’s it like?
Winstead: It was incredibly amazing to see so many people come out in places like Lincoln, Nebraska, and Cincinnati. There were no ads in some towns because the haters would come out. But we would have 400 or 500 people at a show. It was this environment where people would gather and look around and see their neighbors and co-workers. They’d realize, “Oh, we are a force.” Oh, yes, you are.
There were a lot of young women, which was kind of exciting. The goal was to do an event that younger women would enjoy and that was affordable. And we really succeeded. The shows were around 60-65 percent first-time donors. And many under thirty-five. That part made me really happy. Because I had been doing these things sporadically forever and it was always, “We’re having a dinner at $250 a plate, and we are going to honor some people,” and everybody here is seventy. Those people are so valuable, and valued. But, hello? How about people who are fucking? You know, people who can still get pregnant?
To be able to go in and do these Planned Parenthood shows, just talk with politically active people for an entire evening, it’s fun! I mean, how often can you get together and have a salon? It’s really hard to get your own girlfriends together. So to go on the road and get a bunch of women together and start blabbing—that part of it was super fun.
I think people need to adopt Planned Parenthood in their communities. They have to say we are proud this American institution is in our community.
And I think it goes back to the shame thing. When are you going to stop having the shame? It should be like LensCrafters. There should be a Planned Parenthood in every mall. Just like Cinnabon and Chico’s. To me, that would be the utopian society to live in.
Q: Do you ever worry about speaking out?
Winstead: I guess people stay out of the political fray because if you take a polarizing stance, then you are probably not going to be the big giant star that other people who don’t come out swinging are.
And some network executive will say you’re a loudmouth and advertisers will bum out if Suzie-pro-choice activist is on our show. It’s a risk. It’s a risk I’ll take because I feel so strongly about the issue.
Q: Why did you decide to get into stand-up?
Winstead: I was always the class cynic, not really the class clown. I was always running commentary about things, and more often than not people would have a chuckle at something I had to say. One night, a friend and I were having a slumber party, and George Carlin came on TV, and she said, “Why don’t you try that?”
It just never occurred to me. I’d seen older women do it, like Phyllis Diller and Totie Fields, and they talked about their lives. But I never saw a woman in her twenties talking about those experiences. And so I assumed that it was another avenue that was either for men or it wasn’t accepted. Once I realized there wasn’t a reason that I couldn’t do that, I tried it.
It seems like in the last couple of years, this question keeps coming up: Are women funny? If one woman makes a living being funny, then women are funny. That conversation is over. Can we please move on?
Think about the female comedians you like. I would say 95 percent of the women that I love, I didn’t discover them on Letterman. I discovered them on YouTube. Or she was doing some amazing website on her own. Or someone who started her own sketch group. Or something else. It was never waiting for that late night scene. So let it be the old guy dinosaur world. Let them have it. Who cares? We can do our own crap.
Maybe it’s because I turned fifty and I don’t give a shit anymore. Like, what are you going to do to me? I have a really nice life. I’ve done stuff that I’m really proud of. You can develop a really nice career on your own terms. Which is what I’ve done. And it’s kind of fun.
I don’t want to tell jokes to drunks, when a fourth of them just came to the club because it’s a club. And then they get me? What a bummer. So I like to do smaller theaters, which means you do your own press and you have to find the theater and you do your own outreach and it’s crazy.
Q: But it’s worth it?
Winstead: It’s totally worth it. It’s so much fun. I’d rather just die exhausted and fulfilled. That’s all I care about. If I’m tired because I’m working really hard at something I love, OK, great. Because it’s all about the process. Do you think the funnest part of The Daily Show was taping the show? Or taping my Air America show? That was the least interesting part.
The interactions with people, and the insanity of it, and solving a problem, and knowing that you can turn an entire show around on a dime because new news broke at 4:00 and you are taping at 5:00—all that shit’s fun. Seeing people working together and caring about the best idea, and not about their own idea, was fun. It was like a hockey game constantly. A lot of people got to set up. I enjoyed it. I don’t enjoy solitary writing. I enjoy writing with people. It’s way more fun.
Q: Talk about your time in Minneapolis in the “punk rock ghetto.”
Winstead: It was an incredible, creative community. You didn’t have to go to one of the coasts to fail. You could just develop. I don’t know if part of it was that snowy wintertime creative thing, but there were enough of us that we convinced ourselves that we were sort of normal in our weirdness. It was really fun to work at a restaurant with playwrights and musicians. That was normal in New York, but to be in this community that was pumping out as much creative crap as anywhere else was astounding.
As I got older and gained confidence, I realized that I am a creative person. I just am. I’m a talented person who can write a ton of funny shit every day. Like it’s never ending. So, once I got that, you just let a lot of shit go.
Q: Was it exciting to create a new satirical genre with The Daily Show?
Winstead: Yes. It was so crazy. I was finally getting my dream show and it was my first show. I didn’t have the skills. It was only on my instinct. Madeleine Smithberg and I, we developed a format and then they offered me the job to be the head writer. I hadn’t been a head writer on anything. But I wasn’t going to say no. How often does it happen that you get to have your dream show? Turns out several times, but people don’t know that, either.
Most writing staffs have twelve people, and we had six. We had to find the right people. A lot of times that wasn’t necessarily the people who were particularly political on stage. Often it was comics who I thought were really funny or writers who were really funny and were really engaged in the world. A lot of the editors, producers, and some of the writers came from news. We could hit the ground running with everybody’s instinct.
You have to bring an incredible background of knowledge and a background of comedy, because it’s not like writing monologue jokes. Because when something comes up, and you have to write a comedic editorial, you have to know how history repeats, and specific sound bites that were said. It’s a really different medium. And then you have to be able to write for the tone of the show. It’s an incredibly difficult thing to do. Getting tone right is always the toughest thing.
Q: When you worked on The Daily Show did you ever think this was going to be the place where most young people got their news?
Winstead: No, I didn’t. Of course, I couldn’t envision that. I could never have envisioned a media that would devolve so profoundly. The Daily Show is brilliant because it has followed this devolution. If the news gets better, what are you going to make fun of? So the show gets better as the news gets worse. Which is an unfortunate problem in society. Because the media was supposed to be the watchdog for the regular folks, and now comedians have to be the watchdog of the media. So if you have a watchdog for the watchdog, that’s a problem.
But the second I started paying attention, there was no turning back. As I say in the book, it felt like a calling. I had found religion. This weird religion of pointing out this bullshit.
I wonder how things would’ve changed for me or how my life would’ve been if we didn’t have such a derelict media.
If you liked this story by Elizabeth DiNovella, the Culture Editor of The Progressive magazine, check out her story "Wisconsin Women Say They’re Mad as Hell."
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